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UNITED STATES PATENT OFFICE.

was", SUHOLL, OF'nocnsT-oN-TnE-MMN, GERMANY. ASSIGNOR TO FARBWERKE, VORM. MEISTER. LUClUS & BRUNING, 0F Hoons'r- ()NTHE-MAIN, GERMANY, A CORPORATION OF GERMANY.

YELLOW DYE AND PROCESS OF MAKlNG SAME.

Specification-of Letters Patent.

Patented April 24, 1906.

Application filed February 4,1905. Serial No. 244,178. (Specimens-l aliphatic. combining substances, the beta-- diketones of the type of the ethyl aceto acetate. These dyestull's are of a very greenish-yellow shade and mayserve aswool or cot ton d 'estufis, according to the diazo comounr em )10 ed for the combination. I rave found t rat yellow mordant dyestuffs may be obtained if betadiketones of the type in question are combined with the diazo compounds of the ortho-amido salicylic acid and its derivatives and substitution products. While thedyest-ufl's thus obtained produce on wool in an acid-bath compara tively poor shades, they yield )owerful pure yellow lakes if previously mor anted or subsequently treated with metallic salts, es pecially chromium and co per salts. The copper lakes are chiefly lsting'ulshed by their beautiful greenish-yellow shades and re mrtics of fast-ness, especially to light. ucli yellow copper dyestufi's have'hitherto not been known. For the manufacture of these dyestuffs are import-ant derivatives of the beta-kctone aldehydes formed by substitution of the aldehyde hydrogen by an alkyl, alpbyl, alkyloxy, or anilido group. As examples of this class of bodies, but not including them all, may be mentioned ethyl aceto acetate, acetyl acetone, benzoyl acetone and acelio acetic acid anilid (toluidid and xylid) which may be combined with tho diazo compounds of ortho-amido salicylic acid, ortho-an|i(lom.ro-sull'o salicylic acid, para-nitro-o-mnido salicylic acid.

Fxnmplc I: 15.3 kilogramsol'ortho-umido salicylic acid urc dissolved with thirty kilograms of hydrochloric. acid of l. llll'l- \-'])l'lcent. strength in about three hundred liters of water and dlazolised with seven kilograms of, sodium nitrite. The suspension of tho diam compounds thus obtained is run, while stirring, into a solution cooled with ice of fifteen kilograms of eth l accto acetate, 4.7 kilograms of caustic so a, and twent Y kilograms of soda-ash in three hundre liters of water. After standing for several hours the crystalline paste is slowly heated and completely salted out with some common salt. The dyestufl' precipitated as crystals-is then filtered.

Example II: The solution of twenty-two kilograms of the sodium salt of nitro-orthoamido salicylic acid and seven kilo rams of sodium nitrite in about four hundre liters of water is run, while stirring, into thirty kilograms of hydrochloric acid of thirty-per-cent. strength diluted with three times its quantity of water and ice. The diazo compound separates as crystals. After diazotization the whole suspension is run, while stirring, into a solution cooled with ice of eleven kilograms of acetyl acetone, 4.5 kilograms of caustic soda, and twelve kilo rams of sodaash in about three hundred iters of water. The'dyestuff separates as a crystalline brickrcd paste. After some time it is heated, salted out with common salt, and filtered.

Example III: 23.3 kilograms of orthoamido-para-sulfo salicylic acid are dissolved with eight kilograms of caustic soda in about two hundred liters of water. After adding, with stirring, seven kilograms of sodium nitrite the solution is run into thirty kilograms of hydrochloric acid of thirty-per-cent. strength, diluted with some ice and water. The clear solution of the diam com )ound is run, while stirring, into a cooled so ution of fifteen kilograms ethyl aceto acetate, five kilograms of caustic soda, and ten kilograms of soda-ash, or fifteen kilograms of crystalline sodium acetate in about: two hundred liters of water. After some hours the dye solution is slowly heated and salted out. The dyestall separates as acrysta-llino yellow pow or. The dycstull's obtained by this invention are sull'uryellow to brick-red crystalline powders, readily soluble in walcr, their aqueous solutions bcingof a yellow to orangered tint. (in addition of mineral acids the color of the solutions becomes lighter and less intense; on r-ldition of caustic potash, however, darker and brownor. lu concentrated sulfuric acid the color of the solutions corresponds generally to that of the acidified aqueous solution.

Having now described my invention, what I claim is- 1. The process herein described for the manufacture of yellow mordant dyestuffs, which consists in reacting on aliphatic betadiketones with diazo compounds of the orthoalnido salicylic acid.

2. The process herein described for the manufacture of a yellow mordant dyestull, which consists in causing the diazo compound of ortho-amido-sulfo salicylic acid to react on ethyl aceto acetate.

3. As new products the lnordant dyestull's obtained by combining diazotized orthoamido salicylic acid or its substitution products with aliphatic heta dike tones, being sulfurellow to brick-red c *stalline powders,

solu le in water with ycl ow to orange-red color, soluble in concentrated sulfuric acid, insoluble in alcohol and petroleum ether; the mucous solution becoming lighter on addition of mineral acid, but darker on addition of alkali.

4. As a new product, the yellow mordant dyestul'l' having the formula:

obtained by the action of the diazo compound of ortho-amidoara-sulfo salicylic acid on ethyl aceto acetate, in a yellow crystalline powder, readil solub e in water with a yellow color, whic on addition of mineral acids becomes lighter, and darker on addition of alkali, soluble in concentrated sulfuric acid with a greenisluycllow color, insoluble in alcohol and petroleum ether.

In testimony that I claim the foregoing as my invention lhave signed my name in presence of two subscribing witnesses.

F RANZ SCI-IOLL.

Witnesses:

ALFRED Bmsnors, Jonamx' Harness-ram. 

